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01510

Sigma-Aldrich

1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

purum, ≥97.0% (TLC)

Synonym(s):

β-D-Ribofuranose 1-acetate 2,3,5-tribenzoate

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About This Item

Empirical Formula (Hill Notation):
C28H24O9
CAS Number:
6974-32-9
Molecular Weight:
504.48
Beilstein/REAXYS Number:
100243
EC Number:
230-220-4
MDL number:
MFCD00005357
UNSPSC Code:
12352200
PubChem Substance ID:
24844890

grade

purum

assay

≥97.0% (TLC)

optical activity

[α]20/D +44±1°, c = 0.5% in chloroform

mp

128-130 °C

SMILES string

CC(=O)O[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](OC(=O)c3ccccc3)[C@H]1OC(=O)c4ccccc4

InChI

1S/C28H24O9/c1-18(29)34-28-24(37-27(32)21-15-9-4-10-16-21)23(36-26(31)20-13-7-3-8-14-20)22(35-28)17-33-25(30)19-11-5-2-6-12-19/h2-16,22-24,28H,17H2,1H3/t22-,23-,24-,28-/m1/s1

InChI key

GCZABPLTDYVJMP-CBUXHAPBSA-N

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Other Notes

Ribose derivative used for the synthesis of nucleosides[1][2][3][4]; 1-cyanation with Me3SiC

replaced by

Product No.
Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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A. Matsuda et al.
Synthesis, 748-748 (1981)
M. Saneyoshi et al.
Chemical & Pharmaceutical Bulletin, 27, 2518-2518 (1979)
K. Utimoto et al.
Tetrahedron Letters, 23, 237-237 (1982)
A general synthesis of N-glycosides. I. Synthesis of pyrimidine nucleosides.
U Niedballa et al.
The Journal of organic chemistry, 39(25), 3654-3660 (1974-12-13)
Z Tocik et al.
Nucleic acids research, 8(20), 4755-4761 (1980-10-24)
1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (I) was reacted with iodotrimethylsilane (II) and the product, the glycosyl iodide, was coupled with silylated uracil to afford 1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)uracil (III; 89%), with silyated cytosine to afford, on subsequent acetylation, 1-(2,3,5-tri-O-benzoyl-beta-0D-ribofuranosyl)-4-acetamido-2-(1H)-pyrimidinone (IVb; 81%), and with chloromercuri-N-benzoyl-adenine to afford Va

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